S-allyl-laevo-cysteine

S-allyl-L-cysteine

CAS: 21593-77-1 C6 H11 N O2 S MW: 161.22407000 roasted

Identification

NameS-allyl-laevo-cysteine
CAS Number21593-77-1
FDA UNII81R3X99M15
Molecular FormulaC6 H11 N O2 S
Molecular Weight161.22407000
MDL NumberMFCD00151975
Nikkaji NumberJ490.173H

Regulatory

JECFA Food Flavoring1710 S-allyl-L-cysteine
DG SANTE Food Flavourings17.036 S-allyl-L-cysteine
FEMA Number4322
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)21593-77-1 ; S-ALLYL-L-CYSTEINE

Physical Properties

Appearance white to tan powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 1.19100 @ 25.00 °C.
Refractive Index 1.54200 @ 20.00 °C.
Melting Point 214.00 to 216.00 °C. @ 760.00 mm Hg
Boiling Point 300.00 to 301.00 °C. @ 760.00 mm Hg
Vapor Pressure 0.001000 mmHg @ 25.00 °C.
Flash Point 275.00 °F. TCC ( 135.00 °C. )
logP (o/w) 1.310
Shelf Life 12.00 month(s) or longer if stored properly.
Storage refrigerate in tightly sealed containers.
Soluble in water, slightly

Organoleptic Properties

Odor Description at 0.10 % in propylene glycol.

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
IFRA Purity Specification< 0.1% free allyl alcohol
Recommendation for S-allyl-laevo-cysteine usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)30.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA)2.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI)ND (μg/person/day)
NOEL (No Observed Effect Level)250 (mg/kg bw per day)
Threshold of Concern90 (μg/person/day)
Structure ClassIII
baked goods2.00000
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal2.00000
cheese2.00000
chewing gum-
condiments / relishes2.00000
confectionery froastings-
egg products-
fats / oils2.00000
fish products2.00000
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies2.00000
hard candy-
imitation dairy2.00000
instant coffee / tea2.00000
jams / jellies-
meat products2.00000
milk products-
nut products2.00000
other grains-
poultry2.00000
processed fruits-
processed vegetables2.00000
reconstituted vegetables2.00000
seasonings / flavors2.00000
snack foods2.00000
soft candy-
soups2.00000
sugar substitutes-
sweet sauces-

BOC Sciences

Best of Chemicals Supplier

Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...

View All Website 1-631-485-4226 account@bocsci.com

Endeavour Specialty Chemicals Ltd

Expertise in high impact aroma chemicals

Endeavour Speciality Chemicals offers high-impact aroma chemicals, at small to medium scale.

View All Website +44 (0)1327 310 079 enquiries@endeavourchem.co.uk

Glentham Life Sciences Ltd

The Chemical, Biochemical & Research Essentials Supplier

Glentham Life Sciences is a supplier of fine chemicals and raw materials with warehousing, laboratories and packaging facilities in the UK.

View All Website +44 (0) 1225 667798 info@glentham.com

Penta International Corporation

Chemistry innovation

At Penta, our products and services help businesses do business better.

View All Website (973) 740-2300 lisaa@pentamfg.com

Robinson Brothers Limited

Providing Excellence in Chemistry

Award-winning UK chemical manufacturer of chemical intermediates and high-impact aroma chemicals.

View All Website +44 (0)121 553 2451 enquiries@robinsonbrothers.co.uk

TCI AMERICA

Moving Your Chemistry Forward

We continuously strive to advance our technology.

View All Website 1-800-423-8616 Sales-US@TCIchemicals.com;

Potential Uses

FL garlic FL onion FL roasted

Natural Occurrence

garlic garlic bulb onion bulb

Synonyms

S- allyl cysteine S- allyl L-cysteine allyl laevo-cysteine (2R)-3-( allyl thio)-2-aminopropanoic acid S- allyl-L-cysteine S- allylcysteine (2R)-2- amino-3-(prop-2-en-1-yl sulfanyl) propanoic acid (2R)-2- amino-3-prop-2-enylsulfanylpropanoic acid cysteine, S-2-propen-1-yl- L- cysteine,S-2-propen-1-yl- L- deoxyalliin S- prop-2-en-1-ylcysteine S-2- propenyl-L-cysteine S-2- propenyl-laevo-cysteine PubMed: Oral Administration of (S)-Allyl-l-Cysteine and Aged Garlic Extract to Rats: Determination of Metabolites and Their Pharmacokinetics. PubMed: EGFR gene regulation in colorectal cancer cells by garlic phytocompounds with special emphasis on S-Allyl-L-Cysteine Sulfoxide. PubMed: Thermolysis kinetics and thermal degradation compounds of alliin. PubMed: Evaluation of the Effects of S-Allyl-L-cysteine, S-Methyl-L-cysteine, trans-S-1-Propenyl-L-cysteine, and Their N-Acetylated and S-Oxidized Metabolites on Human CYP Activities. PubMed: Alliin Attenuated RANKL-Induced Osteoclastogenesis by Scavenging Reactive Oxygen Species through Inhibiting Nox1. PubMed: Molecular detection and in vitro antioxidant activity of S-allyl-L-cysteine (SAC) extracted from Allium sativum. PubMed: Taste-Active Maillard Reaction Products in Roasted Garlic (Allium sativum). PubMed: Protective Effects of AGE and Its Components on Neuroinflammation and Neurodegeneration. PubMed: PMK-S005 Alleviates Age-Related Gastric Acid Secretion, Inflammation, and Oxidative Status in the Rat Stomach. PubMed: Neuroprotective effect of S-allyl-l-cysteine derivatives against endoplasmic reticulum stress-induced cytotoxicity is independent of calpain inhibition. PubMed: Downregulation of importin-9 protects MCF-7 cells against apoptosis induced by the combination of garlic-derived alliin and paclitaxel. PubMed: Pharmacokinetics of S-Allyl-l-cysteine in Rats Is Characterized by High Oral Absorption and Extensive Renal Reabsorption. PubMed: S-allyl-L-cysteine and isoliquiritigenin improve mitochondrial function in cellular models of oxidative and nitrosative stress. PubMed: Gastroprotective Effects of PMK-S005 against Ethanol-Induced Acute Gastric Damage in Rats. PubMed: Identification of a flavin-containing S-oxygenating monooxygenase involved in alliin biosynthesis in garlic. PubMed: Enzymatic synthesis of γ-L-glutamyl-S-allyl-L-cysteine, a naturally occurring organosulfur compound from garlic, by Bacillus licheniformis γ-glutamyltranspeptidase. PubMed: Effective production of S-allyl-L-cysteine through a homogeneous reaction with activated endogenous γ-glutamyltranspeptidase in garlic (Allium Sativum). PubMed: Metabolism, excretion, and pharmacokinetics of S-allyl-L-cysteine in rats and dogs. PubMed: Garlic γ-glutamyl transpeptidases that catalyze deglutamylation of biosynthetic intermediate of alliin. PubMed: Protective effects of garlic extract, PMK-S005, against nonsteroidal anti-inflammatory drugs-induced acute gastric damage in rats. PubMed: S-allyl L-cysteine protects the retina against kainate excitotoxicity in the rat. PubMed: Development and validation of S-allyl-L-cysteine in rat plasma using a mixed-mode reversed-phase and cation-exchange LC-ESI-MS/MS method: application to pharmacokinetic studies. PubMed: Protective effect of S-allyl-L-cysteine against endoplasmic reticulum stress-induced neuronal death is mediated by inhibition of calpain. PubMed: Retraction. S-Allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells. PubMed: Effect of processing and storage time on the contents of organosulfur compounds in pickled blanched garlic. PubMed: Effects of SAC on oxidative stress and NO availability in placenta: potential benefits to preeclampsia. PubMed: The effects and underlying mechanisms of S-allyl l-cysteine treatment of the retina after ischemia/reperfusion. PubMed: Alliinase from Ensifer adhaerens and Its Use for Generation of Fungicidal Activity. PubMed: The "aged garlic extract:" (AGE) and one of its active ingredients S-allyl-L-cysteine (SAC) as potential preventive and therapeutic agents for Alzheimer's disease (AD). PubMed: [Effect of S-allyl-L-cysteine on isolate heart subject to ischemia/reperfusion]. PubMed: Effects of s-allyl-L-cysteine on cell proliferation and neuroblast differentiation in the mouse dentate gyrus. PubMed: Oxidative insults to neurons and synapse are prevented by aged garlic extract and S-allyl-L-cysteine treatment in the neuronal culture and APP-Tg mouse model. PubMed: Palladium(II) complex with S-allyl-L-cysteine: new solid-state NMR spectroscopic measurements, molecular modeling and antibacterial assays. PubMed: Garlic flavonoids and organosulfur compounds: impact on the hepatic pharmacokinetics of saquinavir and darunavir. PubMed: 3-(allyltrisulfanyl)-2-aminopropanoic acid, a novel nonvolatile water-soluble antimicrobial sulfur compound in heated garlic. PubMed: S-allyl-L-cysteine sulfoxide inhibits tumor necrosis factor-alpha induced monocyte adhesion and intercellular cell adhesion molecule-1 expression in human umbilical vein endothelial cells. PubMed: Protective effects of cysteine analogues on acute myocardial ischemia: novel modulators of endogenous H(2)S production. PubMed: S-allyl L-cysteine diminishes cerebral ischemia-induced mitochondrial dysfunctions in hippocampus. PubMed: Purification and characterization of flavin-containing monooxygenase isoform 3 from rat kidney microsomes. PubMed: Unusual cystine lyase activity of the enzyme alliinase: direct formation of polysulphides. PubMed: Anti-amyloidogenic activity of S-allyl-L-cysteine and its activity to destabilize Alzheimer's beta-amyloid fibrils in vitro. PubMed: Amyloid beta-protein potentiates tunicamycin-induced neuronal death in organotypic hippocampal slice cultures. PubMed: Role of caspase-12 in amyloid beta-peptide-induced toxicity in organotypic hippocampal slices cultured for long periods. PubMed: Two structures of alliinase from Alliium sativum L.: apo form and ternary complex with aminoacrylate reaction intermediate covalently bound to the PLP cofactor. PubMed: S-Allyl-L-cysteine attenuates cerebral ischemic injury by scavenging peroxynitrite and inhibiting the activity of extracellular signal-regulated kinase. PubMed: Structure-activity relationship of neuroprotective and reactive oxygen species scavenging activities for allium organosulfur compounds. PubMed: Dietary S-allyl-L-cysteine reduces mortality with decreased incidence of stroke and behavioral changes in stroke-prone spontaneously hypertensive rats. PubMed: Changes in organosulfur compounds in garlic cloves during storage. PubMed: N-acetylcysteine selectively protects cerebellar granule cells from 4-hydroxynonenal-induced cell death. PubMed: Comparative study of endoplasmic reticulum stress-induced neuronal death in rat cultured hippocampal and cerebellar granule neurons. PubMed: Redox-sensitive proteins are potential targets of garlic-derived mercaptocysteine derivatives. PubMed: In vitro interactions of water-soluble garlic components with human cytochromes p450. PubMed: Aged garlic extract and its constituents inhibit platelet aggregation through multiple mechanisms. PubMed: 1H-15N NMR studies of the complex bis(S-allyl-L-cysteinate)palladium(II). PubMed: Model studies on precursor system generating blue pigment in onion and garlic. PubMed: Aminotransferase, L-amino acid oxidase and beta-lyase reactions involving L-cysteine S-conjugates found in allium extracts. Relevance to biological activity? PubMed: Inhibition of tumor growth by a novel approach: in situ allicin generation using targeted alliinase delivery. PubMed: S-allyl-L-cysteine selectively protects cultured rat hippocampal neurons from amyloid beta-protein- and tunicamycin-induced neuronal death. PubMed: Neurotoxicity induced by amyloid beta-peptide and ibotenic acid in organotypic hippocampal cultures: protection by S-allyl-L-cysteine, a garlic compound. PubMed: Protective effect of S-allyl-L-cysteine, a garlic compound, on amyloid beta-protein-induced cell death in nerve growth factor-differentiated PC12 cells. PubMed: High-performance ion-pair chromatography method for simultaneous analysis of alliin, deoxyalliin, allicin and dipeptide precursors in garlic products using multiple mass spectrometry and UV detection. PubMed: Sulfoxides as urinary metabolites of S-allyl-L-cysteine in rats: evidence for the involvement of flavin-containing monooxygenases. PubMed: Biomonitoring the intake of garlic via urinary excretion of allyl mercapturic acid. PubMed: N alpha-(1-deoxy-D-fructos-1-yl)-L-arginine, an antioxidant compound identified in aged garlic extract. PubMed: Methionine S-oxidation in human and rabbit liver microsomes: evidence for a high-affinity methionine S-oxidase activity that is distinct from flavin-containing monooxygenase 3. PubMed: Allyl-containing sulfides in garlic increase uncoupling protein content in brown adipose tissue, and noradrenaline and adrenaline secretion in rats. PubMed: Species and sex differences in expression of flavin-containing monooxygenase form 3 in liver and kidney microsomes. PubMed: The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins. PubMed: Neurotrophic activity of organosulfur compounds having a thioallyl group on cultured rat hippocampal neurons. PubMed: Cysteine-S-conjugate beta-lyase activity and pyridoxal phosphate binding site of onion alliin lyase. PubMed: Oxidation of cysteine S-conjugates by rabbit liver microsomes and cDNA-expressed flavin-containing mono-oxygenases: studies with S-(1,2-dichlorovinyl)-L-cysteine, S-(1,2,2-trichlorovinyl)-L-cysteine, S-allyl-L-cysteine, and S-benzyl-L-cysteine. PubMed: New agents for cancer chemoprevention. PubMed: Urinary excretion of N-acetyl-S-allyl-L-cysteine upon garlic consumption by human volunteers. PubMed: On the Isolation and Characterization of a C-S-Lyase Preparation from Leek,Allium porrum. PubMed: A novel amino acid glycoside and three amino acids from Allium sativum. PubMed: Interspecific hybrid between Allium cepa and Allium sativum. PubMed: The acute effects of S-(1,2-dichlorovinyl)-L-cysteine and related chemicals on renal function and ultrastructure in the pentobarbital-anesthetized dog: structure-activity relationships, biotransformation, and unique site-specific nephrotoxicity. PubMed: HPLC of S-Alk(en)yl-L-cysteine Derivatives in Garlic including Quantitative Determination of (+)-S-Allyl-L-cysteine Sulfoxide (Alliin). PubMed: Studies on the antimutagenic activities of garlic extract. PubMed: The C-S lyases of higher plants: preparation and properties of homogeneous alliin lyase from garlic (Allium sativum). PubMed: Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein. PubMed: Purification of the alliin lyase of garlic, Allium sativum L. PubMed: gama-L-Glutamyl-S-allyl-L-cysteine, a new gama-glutamyl peptide in garlic.